This intimate documentary explores the life and career of the stage legend Stephen Sondheim through six of his best-known songs.

Fran walks into a piano bar for pizza. She comes back home with Joe, the piano player. Joe plans on winning $5,000 and leave Las Vegas. Fran waits for something else. Meanwhile, he moves in with her.

Trying to shake his troubled past and start a new honest life, Floyd loses his job because of that past. With nowhere to go but back home in Oklahoma he gets news that his father's been murdered and the local sheriff lets the killer off with a self-defense plea. Bent on revenge, Floyd does what he must which leads him down a dark road littered with robbing banks and loose women. Floyd's final days are anything BUT pretty!

In 1970, right after the triumphant premiere of Stephen Sondheim’s groundbreaking concept musical Company, the renowned composer and lyricist, his director Harold Prince, the show’s stars, and a large pit orchestra all went into a Manhattan recording studio as part of a time-honored Broadway tradition: the making of the original cast album. What ensued was a marathon session in which all involved pushed themselves to the limit.